New secondary trisazodyestuffs



Patented May 3, 1932 ERNST FELLMER AND HEINRICH I-IOYER, OF LEVERKUSEN-ON-THE-BHINE, GERMANY,

ASSIGNOBS T GENERAL. ANILINEiWORKS,

TION OF DELAWARE INQ, 0F NEVJ YORK, N. Y., A CORPORA- NEW SECONDARY TRISAZOIDYESTUFFS No Drawing. Anplication filed September 4, 1930, Serial No. 479.792, and in Germany September 11, 1929.

The present invention relates to new secondary trisazodyestufi's, more particularly it relates to dyestuil's of the probable general formula OOOH wherein R and R stand for naphthalene nuclei, and wherein all nuclei may be further substituted by alkyl, oxalkyl or a sult'onic acid group.

tlur new dyestuffs are obtainable by further diazotizing' an ainino-disazo body of the general formula wherein R stands for the residue of salicylic acid or of a derivative thereof, or the residue oi a 1.8-dihydroxynaphthalene-slilfonic acid or a derivative thereof, R stands for the naphthalene nucleus of a diazotized middle connionent of the naphthalene series and R stands for the naphthalene nucleus of a diazotizable middle component of the naphthalene series and couplingin the case where It indicates salicylic acid or a derimtive thereof with a sulfonic acid of 1.8-dihydroxynaphthalene or a derivative thereof and in case where R indicates 1.8-dihydroxynaphthalene-sulfonic acid or a derivative thereof with salicylic acid or a derivative thereof.

()ur new dyestuli's are in the form of their alkali metal salts watersoluble dark powders, dyeing cotton, viscose and mixed fabrics containing viscose grey shades, Which besides a very good fastness to light are distinguished by the technically important property of being unaffected by brightening and of not being boiled oii. Due to the salicylic acid grouping and the 1.8-hydroxynaphthalene residue the dyestuffs are capable of forming copper and chromium lakes in substance or by subsequent treatment on the fiber, which lakes exhibit good fastness to washing; By subsequently treating the direct dyeing with diazotized p-nitraniline a beautiful neutral grey is obtained.

The invention is illustrated by the following examples, without being restricted thereto:

Errmnplc .Z.-15.3 parts by Weight of p-aIninosalicylic acid, after diazotization with hydrochloric acid and 6.9 parts by Weight of sodiinn nitrite, are combined with 22.3

parts by weight of 1-naphthylamine-7. sulfonic acid in a solutionrendercd Weakly acid by means of acetic acid. When the coupling; is complete, the inonoazo dyestuff is further diazotized with 6.9 parts by weight of sodium nit-rite and hydrochloric acid and coupled with 18.0 parts by weight of the hydrochloride of oi-naphthylainiue in the presence of sodium acetate. The resulting amino disazo body is carefully purified by isolation from the solution rendered alkaline, further diazotized at 0 C. with 6.9

parts by Weight of sodium nitrite and coupled with 24; parts by weight of 1.8-dihydroxy- 1151PlItlHIlBHG-l:;Ulffllllt? acid in the presence of sodium acetate or sodium bicarbonate.- The dycstuft having in the free state the following formula:

SOaH 50311 is isolated in the customary manner. It dyes cotton in bluish grey shades, which are unaffected by brightening and which possess very good fastness to light.

Example 2.28.0 parts by weight of acetyl- 1. l-naphthylenediamine-G- (7-) -sulfonic acid are diazotized at 0 C. with hydrochloric acid and 6.9 parts by weight of sodium nitrite and coupled with 24.5 parts by weight of the sodium salt of naphthalene-l-sulfaminic acid in the presence of sodium acetate, further Jdiazotized with hydrochloric acid and 6.9 parts by weight of sodium nitrite and cou pled with cooling with 13.8 parts by weight of salicylic acid in a solution rendered alkaline by means of sodium carbonate. The re action mixture is boiled for half an hour in dilute caustic soda solution in order to split off the acetyl group and the resulting amino disazo body is isolated after neutralization of OOOH We claim:

1. As new products azodyestufis of the probable general formula:

Oooon OH OH OH OH SOaH is isolated in the customary manner; it dyes cotton in greenish blue-gray shades, which are unaffected by brightening and which possess very good fastness to light.

This group of dyestuffs can likewise be built up by diazotizing acyl-1.4naphthylenediamines or sulfonic acids thereof, coupling with salicylic acid, saponifying in caustic alkali solution, further diazotizing and coupling with a middle component of the naphthalene series, diazotizing once again and finally coupling with 1.8-dihydroxynaphthalene sulfonic acid or derivatives thereof.

wherein all nuclei may be further substituted by alkyl, alkoxy or a sulfonic acid group, being in the form of their alkali metal salts watersoluble dark powders, dyeing cotton, viscose and mixed fabrics containing viscose grey shades of good fastness to light which shades are unaffected by brightening and are not boiled off.

CODE

3. As a new product the azodyestufli' of the formula: 1

SOaH S0311 dyeing cotton in bluish grey shades of good fastness to light which shades are unaffected by brightening.

In testimony whereof, we affix our signa- 

